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Organic Chemistry at ABC Chemistry
Organic Chemistry

Master Organic Chemistry with Mechanisms & Reaction Strategy

Comprehensive coverage of reaction mechanisms, retrosynthesis, and synthetic strategies by ABC Chemistry for CSIR-NET, IIT-JAM, GATE & CUET-PG.

Why Organic Chemistry at ABC Chemistry?

Organic Chemistry becomes easy when reactions are understood through electron flow, intermediates, and mechanisms. Our teaching focuses on concept clarity instead of memorization, helping students solve even unfamiliar questions confidently.

Organic Chemistry Syllabus

GOC

Inductive, resonance, hyperconjugation, acidity & basicity.

Stereochemistry

R/S, E/Z, optical activity, conformations.

Reaction Mechanism

SN1, SN2, E1, E2, rearrangements.

Aromatic Chemistry

Electrophilic substitution & directing effects.

Carbonyl Chemistry

Aldehydes, ketones, acids & derivatives.

Named Reactions

Pericyclic & advanced transformations.

GOC & STEREOCHEMISTRY

CSIR June 2011 Question and Answer

Question 1
The configurations at the two stereocentres in the compound given below are:
Stereochemistry question
Correct Answer: (a) 1R,4R

Explanation:
The substituents at each chiral centre are numbered according to the CIP priority rules. The atom with the highest atomic number is assigned the highest priority. After orienting the lowest priority group away from the observer, the sequence of remaining substituents is traced. Both stereocentres show a clockwise arrangement, leading to R-configuration at positions 1 and 4.
Question 2
The two compounds given below are:
Stereochemistry identical compounds
Correct Answer: (b) Identical

Explanation:
A 180° rotation about the carbonyl carbon–carbon bond converts one structure into the other. Since the two structures are interconvertible by simple rotation and no bond breaking is required, they represent the same molecule and are therefore identical, not enantiomers or diastereomers.
Correct Answer: (a) 1R,4R

Explanation:
The substituents at each chiral centre are numbered according to the CIP priority rules. The atom with the highest atomic number is assigned the highest priority. After orienting the lowest priority group away from the observer, the sequence of remaining substituents is traced. Both stereocentres show a clockwise arrangement, leading to R-configuration at positions 1 and 4.
Question 3
In the most stable conformation of trans-1-t-butyl-3-methylcyclohexane, the substituents at C-1 and C-3, respectively, are:
Correct Answer: (c) Equatorial and axial

Explanation:
The t-butyl group is extremely bulky and therefore strongly prefers the equatorial position to avoid 1,3-diaxial interactions. Hence, at C-1 the t-butyl group is equatorial.

Since the substituents are trans-1,3-disubstituted, when one substituent is equatorial, the other must be axial. Therefore, the methyl group at C-3 occupies the axial position.
Question 4
Among the carbocations given below:
Carbocations aromaticity question
Correct Answer: (a)

Explanation:
(A) shows homoaromaticity, where cyclic delocalization is maintained through-space despite interruption in conjugation.

(B) is a planar cyclic system with 4π electrons, which follows the 4n rule and is therefore antiaromatic.

(C) is the cyclopropenyl cation containing 2π electrons, satisfying the Hückel (4n+2) rule, making it aromatic.
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